Water → 2-[4-(4-Acetyl-benzenesulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid methyl ester

HRID 1392947

Reaktionsgleichung

Reaktionsgleichung von HRID 1392947
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:4].[C:16]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)(=[O:18])[CH3:17].C(N(CC)CC)C.O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:11][CH2:12][N:13]([S:25]([C:22]3[CH:21]=[CH:20][C:19]([C:16](=[O:18])[CH3:17])=[CH:24][CH:23]=3)(=[O:27])=[O:26])[CH2:14][CH2:15]2)=[N:7][CH:6]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 2664184-Acetylbenzenesulfonyl chlorideHCID 22831866Methyl 2-(piperazin-1-yl)thiazole-5-carboxylate

Produkt 1

HCID 692013072-[4-(4-Acetyl-benzenesulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid methyl esterAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of compound 11 (200 mg, 0.886 mmol) in dichloromethane (7.5 mL) were added 4-acetyl-benzenesulfonyl chloride (288 mg, 1.320 mmol) and triethylamine (220 mg, 2.169 mmol) under a N2 atmosphere. The reaction mixture was stirred at room temperature for 4 h. Water (10 mL) followed by dichloromethane (10 mL) were added to the reaction mixture and the organic layer was separated, dried on sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using silica gel to give the compound 12h as a solid (346 mg, 96.2%). HPLC: 99.72% (Rt=6.56 min).

Aufarbeitung

  1. additionwere added to the reaction mixture
  2. customthe organic layer was separated
  3. customdried on sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-698439f859754ccd8a8de30b47ed9516
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07345043B2

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